


The Whole Trouble

by reginahalliwell



Category: Gilmore Girls
Genre: F/M
Language: English
Status: Completed
Published: 2014-10-19
Updated: 2014-10-19
Packaged: 2018-02-21 20:08:32
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 674
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2480795
Author URL: https://archiveofourown.org/users/reginahalliwell/pseuds/reginahalliwell
Summary: <blockquote class="userstuff">
              <p>“That's the whole trouble. When you're feeling very depressed, you can't even think.” -J.D. Salinger, The Catcher in the Rye</p>
            </blockquote>





	The Whole Trouble

It had gone too far, past the point of no return, if he thought about it in lame theatrical terms. He watched as his academic career swirled the drain, realizing how bad things had gotten only after he saw them become irreparable.

A part of him knew, in that moment when the prissy girl with the list for prom tickets told him to go to the principal’s office, that he had failed. Not just failed out of school, but he had failed Rory. He failed himself. Jess was too good for this. He couldn’t even graduate from Stars Hollow High.

No, not couldn’t. He could if he had wanted to. He didn’t want to. Right. That was easier.

But he had wanted to. He wanted to make Rory happy, take her to that stupid dance with that stupid tux and music and it sounded awful but he imagined the look on Rory’s face, her in the dress she had most certainly already bought or at least had her mother make. He saw how happy she would be and wanted that for her. He wanted to be the one to make her that happy.

But no, he had to screw it up. This was just one more thing in his life that he had screwed up.

So now, of course, he had made things worse. When he couldn’t deal, with Rory, or with anything, he resorted to being the strong silent type. Broody and mysterious and exceptionally good with his tongue.

But Rory always saw through that. She never accepted his cool exterior—she picked at the walls he put up until she got to the heart of him. He hated that he couldn’t fend her off, that she knew just how to deal with his crap. He also loved it. She gave him hope that he could be better. Could be worth something. Could be good enough for someone like Rory.

Sure, he wasn’t going to Yale. He was her townie boyfriend that she probably should just leave behind. But now he wasn’t even going to be a high school graduate. She was an ivy leaguer. He was a hoodlum, or at least that’s what everyone thought.

God, why had he tried something with her in a random room at some guy’s party? He knew that wasn’t how it was going to happen. He knew they were headed that direction, but he wasn’t dumb enough to think that was the time or the place.

Jess couldn’t wrap his head around everything. Things had gotten so bad so quickly. While it was happening he had tried to ignore it, tried not to see everything he had worked so hard for disappearing. So he disappeared instead. He checked out of everything in his life. Even Rory.

Why on Earth had he taken Rory for granted? He loved her. He had spent a whole year of his life trying to be with her, and then once he got her, once she let him in, he screwed it all up. He stopped being the guy that made her like him in the first place and actually became the guy everybody else saw him as.

He felt so helpless. Watching everything in his life fall apart he could do nothing except crash and burn.

Stars Hollow was supposed to have been a new start for him. Not really, because his reputation had preceded him and he was more than happy to fill the hoodlum sized shoes his mother had shipped there from New York. And now California was a new start too. Except he was leaving the only place he had ever been marginally happy and heading towards the only person who was arguably an even bigger screw up than he was. And he was doing it without Rory.

Rory, who clearly loved him enough to tolerate him. Rory, who believed in him, believed he wasn’t as screwed up as everyone else wanted him to be. Rory was the best thing in his life. And he had destroyed it.


End file.
